Water → HCID 9858421, compound

HRID 395590Notes

Reaction equation

HRID 395590 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[C:6]1([C:12]2[NH:13][C:14]3[C:19]([C:20]=2[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>S(=O)(=O)(O)O>[C:6]1([C:12]2[NH:13][C:14]3[C:19]([C:20]=2[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][C:17]([N+:1]([O-:4])=[O:2])=[CH:16][CH:15]=3)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24268Sodium NitrateHCID 12502667HCID 12502667, compound

Product 1

HCID 9858421HCID 9858421, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 1.19 g (4.10−3 mol) of sodium nitrate in 50 ml of concentrated sulfuric acid is added at 0-5° C., with stirring, to a solution of 3.67 g (13.15.10−2 mol) of 2-pheny-1H-indole-3-butanoic acid in 200 ml of concentrated sulfuric acid. Stirring is maintained at 5° C. for 20 min and the reaction medium is then poured into a mixture of water and ice. The yellow precipitate formed is filtered off and washed on the filter with water and with a small amount of petroleum ether. The product is then dried under reduced pressure and purified by chromatography on silica gel using a hexane/ethyl acetate mixture (1/1) as the eluent to give 1.3 g of the expected product in the form of a yellow solid with a yield of 30%.

Workup

  1. customThe yellow precipitate formed
  2. filtrationis filtered off
  3. washwashed on the
  4. filtrationfilter with water and with a small amount of petroleum ether
  5. customThe product is then dried under reduced pressure
  6. custompurified by chromatography on silica gel using a hexane/ethyl acetate mixture (1/1) as the eluent

Sources & evidence

ORD record
ord-ec1bb5b40f6643d98a611832e6c643cb
Source dataset
uspto-grants-2003_08
Patent number
US06605633B1

Reaction notes

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